JP5006799B2 - 神経疾患及び精神神経疾患の処置用のグリシントランスポーター1(glyt−1)阻害剤としての[4−(ヘテロアリール)ピペラジン−1−イル]−(2,5−置換フェニル)−メタノン誘導体 - Google Patents

神経疾患及び精神神経疾患の処置用のグリシントランスポーター1(glyt−1)阻害剤としての[4−(ヘテロアリール)ピペラジン−1−イル]−(2,5−置換フェニル)−メタノン誘導体 Download PDF

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JP5006799B2
JP5006799B2 JP2007549824A JP2007549824A JP5006799B2 JP 5006799 B2 JP5006799 B2 JP 5006799B2 JP 2007549824 A JP2007549824 A JP 2007549824A JP 2007549824 A JP2007549824 A JP 2007549824A JP 5006799 B2 JP5006799 B2 JP 5006799B2
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methanesulfonyl
phenyl
thiazol
piperazin
methanone
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JP2008526796A (ja
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ヨリドン,ジネーゼ
ナルキジアン,ロベール
ノークロス,ロジャー・ディヴィッド
ピナール,エマニュエル
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F Hoffmann La Roche AG
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • C07D285/02Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/081,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433Thidiazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38Nitrogen atoms
    • C07D277/42Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • C07D285/02Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/121,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • C07D285/02Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/121,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/1251,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
JP2007549824A 2005-01-07 2005-12-28 神経疾患及び精神神経疾患の処置用のグリシントランスポーター1(glyt−1)阻害剤としての[4−(ヘテロアリール)ピペラジン−1−イル]−(2,5−置換フェニル)−メタノン誘導体 Expired - Fee Related JP5006799B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP05100077 2005-01-07
EP05100077.6 2005-01-07
PCT/EP2005/014082 WO2006072436A1 (en) 2005-01-07 2005-12-28 [4-(heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders

Publications (2)

Publication Number Publication Date
JP2008526796A JP2008526796A (ja) 2008-07-24
JP5006799B2 true JP5006799B2 (ja) 2012-08-22

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JP2007549824A Expired - Fee Related JP5006799B2 (ja) 2005-01-07 2005-12-28 神経疾患及び精神神経疾患の処置用のグリシントランスポーター1(glyt−1)阻害剤としての[4−(ヘテロアリール)ピペラジン−1−イル]−(2,5−置換フェニル)−メタノン誘導体

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US (1) US7220744B2 (zh)
EP (1) EP1838308B1 (zh)
JP (1) JP5006799B2 (zh)
KR (1) KR100895752B1 (zh)
CN (1) CN101137363B (zh)
AR (1) AR052866A1 (zh)
AT (1) ATE472327T1 (zh)
AU (1) AU2005324024B2 (zh)
BR (1) BRPI0519794A2 (zh)
CA (1) CA2593463C (zh)
DE (1) DE602005022113D1 (zh)
ES (1) ES2346335T3 (zh)
IL (1) IL184353A (zh)
MX (1) MX2007008189A (zh)
NO (1) NO20073667L (zh)
RU (1) RU2396270C2 (zh)
TW (1) TWI313174B (zh)
WO (1) WO2006072436A1 (zh)
ZA (1) ZA200705472B (zh)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050119251A1 (en) * 2001-12-21 2005-06-02 Jian-Min Fu Nicotinamide derivatives and their use as therapeutic agents
CA2580856A1 (en) 2004-09-20 2006-03-30 Xenon Pharmaceuticals Inc. Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors
TW200626139A (en) 2004-09-20 2006-08-01 Xenon Pharmaceuticals Inc Heterocyclic derivatives and their use as therapeutic agents
AR051294A1 (es) * 2004-09-20 2007-01-03 Xenon Pharmaceuticals Inc Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa
US7951805B2 (en) * 2004-09-20 2011-05-31 Xenon Pharmaceuticals Inc. Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase
BRPI0515483A (pt) * 2004-09-20 2008-07-22 Xenon Pharmaceuticals Inc derivados heterocìclicos para o tratamento de doenças mediadas por enzimas estearoil-coa desaturase
BRPI0611187A2 (pt) 2005-06-03 2010-08-24 Xenon Pharmaceuticals Inc derivados aminotiazàis como inibidores da estearoil-coa desaturase humana
EP2131843B1 (en) 2007-03-05 2011-11-09 F. Hoffmann-La Roche AG Process for the synthesis of glyt-1 inhibitors
WO2010040663A1 (en) 2008-10-09 2010-04-15 F. Hoffmann-La Roche Ag Pyrrolidine n-benzyl derivatives
TW201127806A (en) * 2009-09-02 2011-08-16 Du Pont Process for the synthesis of fluorinated ethers of aromatic acids
TW201127805A (en) * 2009-09-02 2011-08-16 Du Pont Process for the synthesis of fluorinated ethers of aromatic acids
WO2011082660A1 (zh) * 2010-01-08 2011-07-14 中国科学院上海有机化学研究所 5-多氟烷基取代的2-氨基噻唑类化合物、合成方法及其应用
CN101885708B (zh) * 2010-07-07 2013-03-06 中国科学院上海有机化学研究所 5-多氟烷基取代的2-氨基噻唑类化合物、合成方法及其应用
SG186885A1 (en) * 2010-06-04 2013-02-28 Albany Molecular Res Inc Glycine transporter-1 inhibitors, methods of making them, and uses thereof
US9012489B2 (en) * 2011-08-03 2015-04-21 Boehringer Ingelheim International Gmbh Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament
US9266838B2 (en) 2011-08-15 2016-02-23 University Of Utah Research Foundation Substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors
AU2012296804B2 (en) * 2011-08-17 2017-04-20 Remynd Nv Piperazine thiazole derivatives useful in the treatment of tauopathies such as alzheimer's disease
CN104119343A (zh) * 2013-04-25 2014-10-29 苏州科捷生物医药有限公司 2-三氟甲基噻二唑类化合物及其用途
EP3010915B1 (en) * 2013-06-19 2019-05-08 University of Utah Research Foundation Substituted (3-(5-chloro-2-hydroxyphenyl)-1-benzoyl-1h-pyrazole compounds as histone demethylase inhibitors
EP3134406A1 (en) 2014-04-24 2017-03-01 Dart Neuroscience (Cayman) Ltd Substituted 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole and 4,5,6,7-tetrahydro-2h-pyrazolo [4,3-c]pyridine compounds as glyt1 inhibitors
EP3215500A1 (en) 2014-11-05 2017-09-13 Dart NeuroScience (Cayman) Ltd. Substituted azetidinyl compounds as glyt1 inhibitors
CN105712945B (zh) * 2014-12-22 2020-12-01 上海翰森生物医药科技有限公司 2-取代氧基-5-甲砜基芳基哌嗪酰胺类似物及其制备方法和用途
CN105712952B (zh) * 2014-12-22 2021-03-26 上海翰森生物医药科技有限公司 2-取代氧基-5-甲砜基苯基哌嗪酰胺类似物及其制备方法和用途
MA46589A (fr) * 2016-10-24 2019-08-28 Yumanity Therapeutics Inc Composés et utilisations de ces derniers
US11873298B2 (en) 2017-10-24 2024-01-16 Janssen Pharmaceutica Nv Compounds and uses thereof
EP3914593A4 (en) 2019-01-24 2022-11-02 Yumanity Therapeutics, Inc. COMPOUNDS AND THEIR USES
DK3966206T3 (da) 2019-05-10 2023-11-13 Deciphera Pharmaceuticals Llc Heteroarylaminopyrimidinamid-autophagihæmmere og fremgangsmåder til anvendelse deraf
JP2022536540A (ja) 2019-06-17 2022-08-17 デシフェラ・ファーマシューティカルズ,エルエルシー アミノピリミジンアミドオートファジー阻害剤およびその使用方法
CA3188340A1 (en) 2020-08-13 2022-02-17 Boehringer Ingelheim International Gmbh Treatment of cognitive impairement associated with schizophrenia

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB867273A (en) * 1959-02-20 1961-05-03 Wallace & Tiernan Inc Piperazine derivatives
DE2423847A1 (de) 1973-05-28 1975-01-02 Ciba Geigy Ag Neue sulfamoylbenzoesaeureamide
DE2611705A1 (de) 1976-03-18 1977-09-22 Josef Dipl Chem Dr Rer N Klosa N-5-(nitrofurfuryliden-)-1-amino- hydantoin enthaltende kristalloesungsmittel
IT1176613B (it) 1984-08-14 1987-08-18 Ravizza Spa Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione
RU2124511C1 (ru) 1993-05-14 1999-01-10 Фармасьютикал Ко., Лтд Производные пиперазина
JP2002505332A (ja) 1998-03-06 2002-02-19 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ グリシン輸送阻害剤
CN1292698A (zh) * 1998-03-06 2001-04-25 詹森药业有限公司 甘氨酸传递抑制剂
GB0021419D0 (en) 2000-08-31 2000-10-18 Oxford Glycosciences Uk Ltd Compounds
AR032653A1 (es) * 2001-02-09 2003-11-19 Telik Inc Inhibidores heterociclicos del trasportador de glicina 2 composiciones farmaceuticas, uso y metodos.
AU2002344951A1 (en) 2001-07-02 2003-01-21 Boehringer Ingelheim International Gmbh Substituted piperazine and diazepanes as histamine h3 receptor agonists
WO2003035602A1 (fr) 2001-10-25 2003-05-01 Sankyo Company, Limited Modulateurs lipidiques
DE10217006A1 (de) * 2002-04-16 2003-11-06 Merck Patent Gmbh Substituierte Indole
WO2004037800A1 (en) * 2002-10-22 2004-05-06 Glaxo Group Limited Aryloxyalkylamine derivates as h3 receptor ligands
ATE382611T1 (de) * 2003-08-11 2008-01-15 Hoffmann La Roche Piperazin mit or-substituierter phenylgruppe und deren verwendung als glyt1-inhibitoren
RU2355683C2 (ru) 2003-09-09 2009-05-20 Ф.Хоффманн-Ля Рош Аг Производные 1-бензоилпиперазина в качестве ингибиторов поглощения глицина для лечения психозов
CN1874777B (zh) 2003-09-09 2012-07-04 弗·哈夫曼-拉罗切有限公司 作为甘氨酸摄取抑制剂用于治疗精神病的1-(2-氨基-苯甲酰基)-哌嗪衍生物

Also Published As

Publication number Publication date
EP1838308B1 (en) 2010-06-30
EP1838308A1 (en) 2007-10-03
CA2593463A1 (en) 2006-07-13
CN101137363A (zh) 2008-03-05
WO2006072436A1 (en) 2006-07-13
NO20073667L (no) 2007-07-24
RU2007124545A (ru) 2009-02-20
TWI313174B (en) 2009-08-11
CA2593463C (en) 2013-10-08
IL184353A (en) 2012-06-28
AU2005324024A1 (en) 2006-07-13
IL184353A0 (en) 2007-10-31
AR052866A1 (es) 2007-04-11
DE602005022113D1 (de) 2010-08-12
CN101137363B (zh) 2010-09-15
US20060167009A1 (en) 2006-07-27
ZA200705472B (en) 2008-09-25
BRPI0519794A2 (pt) 2009-03-17
ATE472327T1 (de) 2010-07-15
MX2007008189A (es) 2007-08-07
TW200635585A (en) 2006-10-16
KR20070092759A (ko) 2007-09-13
KR100895752B1 (ko) 2009-04-30
US7220744B2 (en) 2007-05-22
RU2396270C2 (ru) 2010-08-10
JP2008526796A (ja) 2008-07-24
AU2005324024B2 (en) 2011-02-17
ES2346335T3 (es) 2010-10-14

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